Planta Med 2005; 71(11): 1058-1062
DOI: 10.1055/s-2005-873129
Original Paper
Natural Product Chemistry
© Georg Thieme Verlag KG Stuttgart · New York

Antimicrobial Azaphilones from the Fungus Hypoxylon multiforme

Dang Ngoc Quang1 , 4 , Toshihiro Hashimoto1 , Marc Stadler2 , Niko Radulović3 , Yoshinori Asakawa1
  • 1Faculty of Pharmaceutical Sciences, Tokushima Bunri University, Tokushima, Japan
  • 2Bayer Health Care AG, PH-R&D-R-EU-ET1, Wuppertal, Germany
  • 3Department of Chemistry, Faculty of Sciences and Mathematics, University of Nisˇ, Nisˇ, Serbia and Montenegro
  • 4Faculty of Chemistry, Hanoi University of Education, Hanoi, Vietnam
Dedicated to Prof. Dr. Adolf Nahrstedt on the occasion of his retirement from Planta Medica
Further Information

Publication History

Received: October 31, 2004

Accepted: May 27, 2005

Publication Date:
17 October 2005 (online)

Abstract

Four new azaphilones named multiformins A - D together with a known compound 4 : 5:4′:5′-tetrahydroxy-1 : 1′-binaphthyl were isolated from the methanolic stromatal extract of the xylariaceous ascomycete Hypoxylon multiforme. Their absolute structures were characterised by 2D-NMR, UV, IR, mass and CD spectroscopy. Multiformins A - D showed strong and apparently non-selective antimicrobial activity.

References

  • 1 Tabata Y, Ikegami S, Yaguchi T, Sasaki T, Hoshiko S, Sakuma S, Shin-Ya K, Seto H. Diazaphilonic acid, a new azaphilone with telomerase inhibitory activity.  J Antibiot. 1999;  52 412-4
  • 2 Tomoda H, Matsushima C, Tabata N, Namatame I, Tanaka H, Bamberger M J. et al . Structure-specific inhibition of cholesteryl ester transfer protein by azaphilones.  J Antibiot. 1999;  52 160-70
  • 3 Matsuzaki K, Tahara H, Inokoshi J, Tanaka H, Masuma R, Omura S. New brominated and halogen-less derivatives and structure-activity relationship of azaphilones inhibiting gp120-CD4 binding.  J Antibiot. 1998;  51 1004-11
  • 4 Yoshida E, Fujimoto H, Baba M, Yamazaki M. New azaphilone metabolites isolated from ascomycetous fungi, Talaromyces luteus and T. helicus .  Tennen Yuki Kagobutsu Toronkai Koen Yoshishu. 1993;  35 290-7
  • 5 Thines E, Anke H, Sterner O. Trichoflectin, a bioactive azaphilone from the ascomycete Trichopezizella nidulus .  J Nat Prod. 1998;  61 306-8
  • 6 Stadler M, Anke H, Dekermendjian K, Reiss R, Sterner O, Witt R. Novel bioactive azaphilones from fruit bodies and mycelial cultures of the Ascomycete Bulgaria inquinans (Fr.)  Nat Prod Lett. 1995;  7 7-14
  • 7 Anke H, Kemmer T, Hoefle G. Deflectins, new antimicrobial azaphilones from Aspergillus deflectus .  J Antibiot. 1981;  34 923-8
  • 8 Hashimoto T, Asakawa Y. Biologically active substances of Japanese inedible mushrooms.  Heterocycles. 1998;  47 1067-110
  • 9 Quang D N, Hashimoto T, Nomura Y, Wollweber H, Hellwig V, Fournier J. et al . Cohaerins A and B, azaphilones from the fungus Hypoxylon cohaerens, and comparison of HPLC-based metabolite profiles in Hypoxylon sect.  Annulata Phytochemistry. 2005;  66 797-809
  • 10 Quang D N, Hashimoto T, RadulovicŽ N, Fournier J, Stadler M, Asakawa Y. Sassafrins A - D, new antimicrobial azaphilones from the fungus Creosphaeria sassafras .  Tetrahedron. 2005;  61 1743-8
  • 11 Stadler M, Wollweber H, Mühlbauer A, Henkel T, Asakawa Y, Hashimoto T. et al . Secondary metabolite profiles, genetic fingerprints and taxonomy of Daldinia and allies.  Mycotaxon. 2001;  77 379-429
  • 12 Takahashi M, Koyama K, Natori S. Four new azaphilones from Chaetomium globosum var. flavo-viridae .  Chem Pharm Bull. 1990;  38 625-8
  • 13 NCCLS (National Committee for Clinical Laboratory S tandards). Performance standards for antimicrobial disk susceptibility testing, 6th International Supplement. Fort Wayne; Wayne Publishing 1997: pp M2-A6
  • 14 Smith-Palmer A, Stewart J, Fyfe L. Antimicrobial properties of plant essential oils and essences against five important food-borne pathogens.  Lett Appl Microbiol. 1998;  26 118-22
  • 15 Rodriguez E, Towers G HN, Mitchell J C. Biological activities of sesquiterpene lactones.  Phytochemistry. 1976;  15 1573-80
  • 16 Stadler M, Wollweber H, Fournier J. A new species of Hypoxylon in France, and notes on the chemotaxonomy of the ”Hypoxylon rubiginosum complex”.  Mycotaxon. 2004;  90 187-211

Yoshinori Asakawa

Faculty of Pharmaceutical Sciences

Tokushima Bunri University

Yamashiro-cho

Tokushima 770-8514

Japan

Fax: +88-655-3051

Email: asakawa@ph.bunri-u.ac.jp

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